Silyl triflate-accelerated additions of catalytically generated zinc acetylides to N-phenyl nitrones

被引：13

作者：

Downey, C. Wade ^{[1
]}

Maxwell, Erin N. ^{[1
]}

Confair, Danielle N. ^{[1
]}

机构：

[1] Univ Richmond, Richmond, VA 23173 USA

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 35期

基金：

美国国家科学基金会;

关键词：

Zinc acetylides; Nitrones; Silyl triflates; Propargyl amines; TERMINAL ALKYNES; ALKYNYLZINC REAGENTS; ASYMMETRIC ADDITION; BETA-LACTAMS; HYDROXYLAMINES; AMIDES;

D O I：

10.1016/j.tetlet.2014.07.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Terminal alkynes readily form zinc acetylides in the presence of iPr(2)NEt and 20 mol % ZnBr2, then attack N-phenyl nitrones activated by trimethylsilyl trifluoromethanesulfonate. Deprotection with aqueous acid yields N-hydroxyl propargylamine. Yields are generally high for nitrones derived from aromatic aldehydes. Control experiments suggest that silyl triflate has a significant accelerating effect upon the reaction. (C) 2014 Elsevier Ltd. All rights reserved.

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收藏

页码：4959 / 4961

页数：3

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